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Caitlin Iseler of ‘happyly’: “Follow your heart and don’t be afraid to ask for help”

Follow your heart and don’t be afraid to ask for help. There are so many people that have been there, done that, and are genuinely happy to offer guidance. As a part of our series about strong women leaders, we had the pleasure of interviewing Caitlin Iseler, mom, former technology executive and now, founder of […]

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Follow your heart and don’t be afraid to ask for help. There are so many people that have been there, done that, and are genuinely happy to offer guidance.


As a part of our series about strong women leaders, we had the pleasure of interviewing Caitlin Iseler, mom, former technology executive and now, founder of happyly — the family adventure planning app..

Caitlin Iseler, happyly founder and CEO, was born in New York, attended the University of Virginia and was a member of the National & ACC Championship Teams. Caitlin and her family live in Jackson, Wyoming. She is married to Thomas and they have three children that bring them great joy.


Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I spent 15 years working with technology companies advising founders as they built teams and made their dreams a reality. Then, when my daughter was born and I was spending hours researching how we would spend our time together, I thought, there must be a better way. Parents are busy and bringing the best practices from other industries to help families get off their screens and safely into the world became a personal priority.

Can you share the most interesting story that happened to you since you began leading your company?

I was laid off from my job in May in the height of COVID’s corporate strain, seemingly the worst time to take a passion project and make it a business, but it was truly meant to be. Without that nudge, I’m not sure I would have had the courage to leave a career I had built over the course of 15 years. I’ve enjoyed more time for my family and the headspace to build something that, we hope, will make a difference for families everywhere.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’ve made so many, where do I start? I really underestimated how long it takes to build something good. I’m not sure it’s funny but it’s certainly been humbling and it’s taught me so much patience.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Can I list like 50 people? I have been the recipient of so much kindness, in life and while building happyly with a team that blows my mind every day. The moms, dads and grandparents that have contributed to making happyly real are the most incredible people. My dream is to get them all together in person someday in Jackson, WY as a small token of my gratitude for all they have poured into happyly and our community.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I’m obsessed with the Peloton Yoga Anywhere series. I’ve been an inconsistent Peloton spinner but Yoga Anywhere requires no yoga mat or proper attire and only takes 10 minutes. It’s the simple act of remembering to breathe and be present that has made a huge difference for my mental health.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality, and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Diversity comes in many different forms and for me, diversity of life experiences is one of the most important criteria for ensuring we are on the right track. Our team consists of people from all over the country with a variety of cultural, academic and socioeconomic backgrounds, sexual orientations, and approaches to faith. What bonds us is the alignment of our values — the only thing we don’t want to be diverse — caring for the world and others, an innate belief in doing the right thing, a commitment to authenticity and leading with love.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

My favorite work culture was described as a meritocracy and that’s the kind of culture we have built and continue to develop at happyly. It doesn’t matter your role, where you went to school, your age, whether you are part-time or full-time, the best idea wins and hard work is how respect is earned and maintained.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

At 38, I know what I’m good at, I know where I struggle and I’m content being me. Why does this matter? Because as a CEO, it’s my job to surround myself with people that are different from me and that have different strengths to ensure our collective impact is most powerful. Our Co-founder and COO is exceptional with details and compliance, our Editor In Chief and Co-Founder is a wizard with words and detail, our Head of Community Marketing brings discipline regarding the process and our CTO always sees the long term and gets ahead of problems.

For me, I thrive when I can be creative and spend time with people building relationships whether with our team and our growing community or with companies that we have the pleasure of working with. We are blessed with an advisory team that humbles me every day, they are experienced, patient, and wise and it’s been such a gift to have so many diverse perspectives that truly make us the company we are today.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

You’re expected to be the authority or know everything. This is my second role as a founder and the most important lesson I learned (the hard way) is that I don’t need to know everything. I need to listen to the experts and let each person on our team do their job and be empowered to make decisions.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Fundraising has been historically an issue for women executives but we have been really fortunate to have support in this capacity. We’ll see what happens when we start the institutional round in a few weeks, fingers crossed!

What is the most striking difference between your actual job and how you thought the job would be?

It’s honestly a dream job. I feel like I’m living my purpose and learning so much every day, working with people I love and respect. I spend more time on pitching our business than I thought but that’s been a great learning experience too!

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Evaluating executive talent for my clients for fifteen years was a lot of fun. I think humility and the ability to put things in perspective is easier said than done but is such an important factor for lasting success. My long-time advisor always tells me, “This is a moment in time,” and it’s advice I repeat to myself often.

What advice would you give to other women leaders to help their team to thrive?

Follow your heart and don’t be afraid to ask for help. There are so many people that have been there, done that, and are genuinely happy to offer guidance.

How have you used your success to make the world a better place?

I certainly hope to! We are in our early days but even the smallest bits of positive feedback regarding the benefits of what we’ve built from a parent or company is so gratifying — it means everything to know we’ve made a difference for someone’s family.

What are some of your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Building an app is super complicated! We’ve learned over time what a good development partner looks like and we are so fortunate to have found our way to the team at Melt. They are incredibly talented and are making our vision a reality.
  2. Patience is so important — the best version of anything is bound to take time!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be?

You never know what one idea can trigger. Happyly is focused on getting families off their screens and into the world together. It is my dream that raising a generation of children that will have easy access to hiking, playgrounds, and other healthy alternatives to screen time will make them happier and more productive people long term.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Building a business is a marathon, not a sprint. I am and have always been all in. I know one speed, fast! That said, I’ve learned that in business, as in life, all good things take time and consistent effort.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I think Richard Branson is fascinating and I admire his ability to balance creative, solid business principles with caring deeply about the world.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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