Finding My Work Soulmates at Leap.

November 3, 2021

Finding My Work Soulmates at Leap.

May 29, 2023

I have known for a long time that I wanted to create meaningful connections for the generations above mine – I just didn't know exactly what to build to make that happen. So, I did what most entrepreneurs do – I talked to potential users and reached out to anyone who was active in this space.

It didn't take long until the name Chip Conley started to come up. Luckily, one of the people he famously 'menterned' at AirBnB was a friend of mine and we were introduced. Looking back at that first conversation with Chip, I am amazed that he continued to answer my emails. The ideas I had were bad. My passion, though, was (and still is) very real. Chip recognised that.

In addition to great advice, Chip invited me to the MEA Facebook group and encouraged me to ask MEA members to try out the tests I was running. I have come to realise that this generosity and open-minded spirit runs through everyone and everything at MEA.

One of our first users was Anita Baker, an MEA Alum, who joined our photography class. There were so many flaws with this experience, but there was also a spark of what has since become Leap – our ever-evolving social learning platform. Thankfully, Anita saw our potential – and came along for the ride, continuing to try out our experiences, classes and conversations on various topics. She always shared her feedback, asked thoughtful questions, and came back with suggestions for improvements.

Today, Anita runs partnerships at Leap.

Only that is not entirely true.

In reality, what she does goes far beyond partnerships.

"Who are your early adopters, Caroline?"
"Why do you think they would be a good partner?"
"Why do you think we can grow like this?"
"Why is this the right way to monetize?"

Anita asks questions. Not only does she ask questions, she also questions me in a truly positive way. As a young, start-up CEO, you can easily get used to people doing what you say and not asking why you say it. It takes more than confidence to ask why. It takes a combination of experience, wisdom and curiosity. The experience of seeing people and companies going down the wrong path; the wisdom to understand why we do certain things; and the curiosity to explore this and come back armed with solutions.

I find very few people of my own Millennial generation asking the vital question – why?

We have now started to grow our community of experienced, wise, creative and curious thinkers and invited many of them to join us as Leap Leaders. Our Leap Leaders host various activities for our users - from workshops on anything from journaling, poetry and philosophy – to conversations on kindness, travel, current affairs and just about everything in between.

We have had electrifying talks on the inauguration, on relationships, on blame, on what's happening in Afghanistan, on movies and films. The list is endless. What is not endless is the number of participants. At Leap, we always meet in small groups of five to ten as we believe this is how the most meaningful connections are created. Small groups, big conversations.

I encourage everyone starting, growing or running a business to find their own modern elder – their very own Anita – if they are lucky enough to find one. Simply put, things work better this way. I work better this way. And Leap works better this way.

If you want to get in touch or have questions on “why?”, feel free to send me a note at If you have ideas for Leap partners send Anita a note at

We look forward to having a conversation with you.

Caroline Ingeborn, 39, is a Swedish serial entrepreneur and the CEO of, a social learning platform for people 55+. Anita Baker, 67, leads her own consultancy, Collaboration Life which focuses on business development, partnerships and growth strategies and is the Modern Elder Academy North Bay Chapter lead.

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