Matthew Dicks can tell a good story. He’s got plenty of material—he’s been brought back from the dead twice, jailed, homeless, and rescued from a fire. The celebrated local author, educator, and entrepreneur is quick to admit his “really odd and unfortunate life” is an open book. He’s also passionate about his many careers and adamant about saying yes to opportunities.

For example, in 2011 friends encouraged Matt to tell a story at The Moth in New York, which encourages the art and craft of storytelling. “I said yes even though I never wanted to do it,” he admits. “I was terrified.”

Matt won the storytelling competition the first night and subsequently fell in love with the process. Two years later, Matt and his wife, Elysha, started Speak Up, a Greater Hartford-based storytelling organization.

Matt met with Innovation Destination Hartford Website Curator Nan Price in his fifth grade classroom at Wolcott Elementary School in West Hartford. There, they discussed entrepreneurship, storytelling, and Matt’s system of keeping life in balance.

NP: Tell us about the first Speak Up show.

MD: It was February 2013. I called Real Art Ways and pitched my idea to Executive Director Will Wilkins. He said: It’s a snow day. There’s no one here. Why don’t you come over?

So I met with Will and told him what I wanted to do. He asked: What’s the name of your organization? I said: I don’t have one. He said:  Who are your storytellers? I said: I don’t have any. He said: Well, you have a date, you have a location. You should get a name and get some storytellers.

I remember walking out the door thinking: That’s a really smart guy. That’s an excellent to-do list for me.

NP: Fast forward two months to April 2013—your first show.

MD: When we arrived that night, LB Muñoz, who was running events at Real Art Ways at the time, asked: How many chairs should I put out? I said: We have eight storytellers and all of them will probably bring a friend, so that’s 16. And Elysha and I make 18, so 20 or 30.

She said: I’m going to put out 90. And I thought: No! Empty chairs kill a show. I thought she had ruined us from the start. But we had more than 150 people come that night.

NP: How has Speak Up evolved since?

MD: The stories were good that first night. We’re much better now. We didn’t curate back then. Now every storyteller goes through a process with us. They never take the stage before we know what they’re going to say. And we’ve really help them craft their stories.

NP: Since 2013, you’ve developed partnerships with Real Art Ways, Infinity Hall, The Connecticut Historical Society, The Mount, and the Noah Webster House, to name a few.

MD: It’s been great. We approached Real Art Ways, which we think of as our home—they’ve really accepted us. All of those other partnerships came to us. Connecticut Historical Society Program Manager Jenny Steadman coordinates rotating exhibits. She wanted to launch each exhibit with related stories, so Speak Up matches a theme to each exhibit.

The Connecticut Historical Society became the place where I teach storytelling. I used to do it here in my classroom and at Real Art Ways. I also teach at the Kripalu Center for Yoga & Health in The Berkshires. But I mostly teach the Connecticut Historical society.

Infinity Hall also came to us, as did The Mount in Lenox, MA—which is the home of American author Edith Wharton. We do one or two shows a year there.

NP: And these connections have all been word-of-mouth?

MD: Yes. We don’t do any marketing. We haven’t actively sought any partners, they’ve come to us. Over the years, we’ve developed partnerships with the Universalist Unitarian Society in Manchester, the Mandell Jewish Community Center of Greater Hartford, and CT Voices of Hope.

We’re at a point where we turn places down all the time because we have enough venues in the Hartford area, so we’re not looking for new ones. We’re sort of maxed. We do about a show a month. I think we did 17 last year.

NP: You mentioned you also teach storytelling.

MD: Right. I also work with corporations and I consult with individuals—filmmakers and storytellers and writers—people who want to rebrand themselves and their companies. I life coach people, too. I have regular clients I speak to once a month.

And I’ve worked with West Hartford public schools and Windsor public schools teaching principals and administrators how to tell stories of their school systems.

Over the last three years, I’ve developed a real hard-core curriculum in terms of storytelling, and I just sold a book about storytelling.

As a teacher for 20 years, and a storyteller of some renown, those two things have combined for me. So I understand how to spiral curriculum. I understand how to break large concepts into small concepts. I know what should flow into what. I understand the value of practice.

NP: You wear so many hats— author, teacher, public speaker, life coach—how do you keep all your balls in the air?

MD: I focus on one ball at a time. Trying to keep all the balls in the air is crazy!

NP: So all the balls are on the ground and you’re just picking up one at a time—I really like that concept.

MD: Right. The juggling doesn’t make any sense. I try to create systems in my life where I can do things without taking up too much of my mental or physical energy. That works out well for me.

NP: What does your entrepreneurial identity mean to you? Do you think of yourself as an entrepreneur?

MD: I do. My advice to everyone is: Whatever your job is, whatever your career is, you should be devoting somewhere between 10% and 15% of your time on your next career.

You may not see it as a career. When I went to The Moth in July 2011, I didn’t know I was starting a new career, but I truly was. When I wrote my first novel, I never expected it to get published. I didn’t think I was starting my next career. But I was dedicating a portion of my time to something other than my job.

I’m just always looking for the next thing. The unfortunate thing for me is I never leave the first thing. I’ve been teaching at Wolcott for 20 years. I love teaching kids. I tend to just add careers onto the career I have—I’m not sure if that’s necessarily advisable.

NP: So, you’re a career hoarder?

MD: My wife says I “collect jobs.” There’s a lot of truth to that. And part of it is because there was a time when I was homeless. I truly never thought I was going to get off the streets.

So I’m constantly trying to ensure that no matter whatever happens in my life, I will have other ways to support my family. It comes with a balance—I have to make sure if I’m going to everything I do I’m also spending time with my family.

But yes, I do think of myself as an entrepreneur. I’m always looking for that next thing.

NP: How have your life experiences shaped your entrepreneurial journey? Any challenges you can share?

MD: I really enjoy talking to people. I think of storytelling as making the world a more interesting place. When I teach storytelling, I like to think I’m helping people become more interesting. And by telling stories I open my heart. I make connections. I get closer to people.

As far as challenges, I know I can often command more money than I do. When people ask me how much I charge, whatever number I put out there, I always know I should say twice as much. And I know many times they will say yes.

I have a literary agent and a speaking agent. I always make more money when the agents are involved because they always advocate for me.

It’s a really challenging thing. If I was making widgets and putting them on a shelf, that would be different. But I’m doing something I think is valuable and important, and therefore I just feel uncomfortable when I ask for a lot of money.

That’s been one of the hardest things along the path. Another challenge I’ve discovered is that I say yes to everything. That’s my policy.

People think it’s crazy. But I can’t tell you how often a crazy yes spins off into something really beneficial and profitable—it causes me to make a connection with someone who will help me down the road.

I say yes because who knows what may happen? There could be a television producer in one of my audiences. I know I can turn a yes into a no, but to just cut off the yes initially is a bad idea.

To learn more about Matthew Dicks and Speak Up visit Follow Matt on Twitter at @MatthewDicks. Follow Speak Up on Facebook.