Caitlin Iseler of Happyly: “Women are amazing problem solvers”

Women are amazing problem solvers. Businesses are about solving an issue and serving a specific purpose, whether professionally related or for something in your everyday life. If you identify a problem, being a founder is such an amazing opportunity to be part of the solution. You never know whose life you will positively impact. As […]

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Women are amazing problem solvers. Businesses are about solving an issue and serving a specific purpose, whether professionally related or for something in your everyday life. If you identify a problem, being a founder is such an amazing opportunity to be part of the solution. You never know whose life you will positively impact.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Caitlin Iseler.

Caitlin Iseler is the founder and CEO of happyly and created an app with her closest mom friends to help parents find 5-star family experiences in under 60 seconds. Caitlin and her family live in Jackson, Wyoming and love being outside together.


Thank you so much for doing this with us! 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?

Before starting happyly, Caitlin worked with private equity back technology companies in executive search with Korn Ferry and her own firm that she later sold. She found her purpose in the intersection of supporting working parents and leveraging technology to save parents time so they can focus on what’s most important, making the moments count with those they love. Caitlin and the happyly team believe deeply in the power of the outdoors to find joy and connection and decrease burnout and depression short and long term. As a mom juggling work and family, Caitlin became obsessed with lifting the mental load and helping every parent feel like a superhero parent.

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

Starting happyly has been the most incredible journey filled with humbling moments. The best part has been meeting the incredible people that have become ambassadors, real parents out every day trying to give their families the best.

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?

Initially we named the company Happy Active Family. When my best friend couldn’t remember the name, I figured we should probably change it. Humbling to have something be so clear in your head and then not have it stick for others.

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?

Our lead investor, Michael Berkman, believed in this idea before it was real. He was the first one to suggest we commit to building happyly and fundraise to fulfill this wild dream. I’ve known Michael and his wonderful wife, Jeannien, for almost 10 years. Back when I worked in Executive Search, they gave me many opportunities to recruit for their team, an acquisition and the chance to help lead talent for one of their companies. When I had this out-of-the-box idea, they gave me the gift of their time, listening and allowing me to ideate without judgment or pressure to have all of the answers all of the time. These early dinners and coffee talks were highlights for me and provided an encouraging space to create. Michael and Jeannien are friends to my husband and I, and inspiring mentors — I couldn’t be more grateful.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies? Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

The fundraising world can be such a black box. Transparency around how it works and what needs to happen for investors, grants and development programs to launch entrepreneurs is so important. I have a good friend, Jason Caplain, who is an investor (Bull City Venture Partners). Jason has taken my calls, answered my crazy questions and always given me so much real feedback. I know that his company has predetermined requirements, a stage at which they’ll invest and specific locations businesses need to be — there’s no grey area. It’s so refreshing and I hope more of the investment world takes this approach.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Women are amazing problem solvers. Businesses are about solving an issue and serving a specific purpose, whether professionally related or for something in your everyday life. If you identify a problem, being a founder is such an amazing opportunity to be part of the solution. You never know whose life you will positively impact.

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

It’s so interesting to hear stories on NPR’s How I Built This and other incredible podcasts about successful founders. It’s so important to realize that almost zero were overnight successes. I’m always humbled to hear that a company like Alltrails took 15 + years to get the traction they enjoy today and to become a household name.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

No. You have to be built for the stress, resilient enough to survive the hard times and persistent beyond belief. Success is not guaranteed and every day someone will tell you your idea stinks (not always in words). You have to believe in yourself in the craziest way (and be lucky enough to be surrounded by people who remind you on the days that it’s hard to do).

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.) How have you used your success to make the world a better place?

We’re creating flexible jobs for moms and dads and hope to create more every week as we grow. We believe you can have a rewarding job and earn income without sacrificing the kind of parent you want to be. Our team is an amazing mix of stay-at-home moms, grandparents and full-time parents that write with us as a creative outlet. The bond is that we all believe in the power of getting kids outside and enjoying the moments of parenthood.

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 your idea can trigger.

I hope that parents remember that the best thing you can spend on your children is time. I’m a big believer that instilling love in nature and showing them that you can be present with them whether on a family hike, bike ride or exploring a new playground is more valuable than anything material.

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.

Private lunch- Guy Raz from NPR, how I built this. His interviews with founders and entrepreneurs are constant inspiration and I learn so much from every episode. He’s inspiring, authentic and asks exceptional questions that give so much to me and all entrepreneurs looking to make a difference.

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

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