Genuine Connection Changes Everything
Cheryl Dillon is a connection expert who helps people transform how they work, lead, and live.
The Heart Behind Funderful
Hi, I’m Cheryl Dillon, the founder of Funderful Experiences.
I believe genuine connection with others is the single greatest driver of both our happiness and business success.
Whether I’m working with a professional, a local business, or a circle of women in midlife, I help people move beyond small talk into something deeper, more meaningful, and truly Funderful.

For Local Businesses:

For Women in Midlife:

True friendship in midlife is harder to find than most people admit.
Connected Hearts was built for exactly that – a community for women who want something real – depth, fresh perspective, and a place where you can be yourself, feel seen, and finally belong.
Connected Hearts is an in-person community in North County San Diego, with an online community launching soon.
In Their Own Words
Cheryl’s talk on the Power of Genuine Connection was one of the most fun and interactive presentations we’ve had at Rotary. She has a rare ability to speak straight to the heart – her humor, authenticity, and practical wisdom left me with a new perspective on how I show up in my conversations. I’d recommend her to any group looking for a speaker who helps people truly connect while having fun doing it.
Cheryl’s presentation was fabulous – engaging, practical, and honestly a lot of fun. She gave us real tools for going beyond surface-level chatter and building genuine connections, from how to ask better questions and remember the details that matter, to how to gracefully exit a conversation with someone who can’t stop talking about themselves.
I made a new connection right away during the exercises. If your organization is looking for a speaker who is warm, funny, and genuinely changes how people interact with each other – invite Cheryl.
I’ll be honest, when Cheryl started leading us through some of the exercises, I wasn’t sure what to expect. It felt a little outside my comfort zone at first. But once we got into it, the value became crystal clear. Two months later, I’m still using what I learned that day in my conversations.Cheryl has a gift for making practical, meaningful skills genuinely accessible, and even fun. I’d recommend her to any group that wants to walk away with tools they’ll actually use.
Connected Hearts has reinforced for me that there is a community of support, friendship, and laughter out there if you open yourself up to it.Participating is like receiving a superhero cape. It makes me feel brave, but also wrapped in comfort and warmth.
I’ve always wanted to be a better conversationalist, but I didn’t know where to start. Cheryl broke down the actual mechanics of building a real connection with someone you’ve just met. She’s enthusiastic, relatable, and so easy to listen to. I’d recommend this to anyone who wants to communicate more deeply and move past surface-level relationships.
There’s a warmth and authenticity here that’s hard to find. I’m so grateful this community exists.
I recently moved to Carlsbad and was looking for ways to get closer to people. Cheryl gave me real tools for doing exactly that. She’s warm, funny, and so sincere. If you want to deepen even a casual acquaintance into something more meaningful, this presentation is for you.








